Potassium bisulfate → Tert-butyl N-(1-oxohex-4-YN-2-YL)carbamate

HRID 342146ノート

反応式

HRID 342146 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([NH:14][CH:15]([CH2:22][C:23]#[C:24][CH3:25])[C:16](N(OC)C)=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8].S([O-])(O)(=O)=O.[K+]>CCOCC.O>[C:7]([O:11][C:12]([NH:14][CH:15]([CH2:22][C:23]#[C:24][CH3:25])[CH:16]=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8]

参加物

6

反応物 3

HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 21258867Carbamic acid, [1-[(methoxymethylamino)carbonyl]-3-pentynyl]-, 1,1-dimethylethyl ester

生成物 1

HCID 45092115Tert-butyl N-(1-oxohex-4-YN-2-YL)carbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

A suspension of lithium aluminum hydride (1.56 g, 41.1 mmol) in ether (150 mL) was stirred at room temperature for 30 minutes. The solution was cooled to -55° C. under nitrogen, and a solution of the product from Step E (11.10 g, 41.1 mmol) in ether (150 mL) was added over 15 min, maintaining the temperature below -50° C. When the addition was complete, the reaction was warmed to 5° C., then recooled to -40° C. A solution of potassium hydrogen sulfate (21.8 g) in 25 mL water was slowly added, maintaining the temperature below -35° C. The mixture was warmed to room temperature and stirred for one hour, filtered through Celite, and concentrated in vacuo to provide the title aldehyde.

後処理

  1. temperatureThe solution was cooled to -55° C. under nitrogen
  2. temperaturemaintaining the temperature below -50° C
  3. additionWhen the addition
  4. temperaturethe reaction was warmed to 5° C.
  5. customrecooled to -40° C
  6. temperaturemaintaining the temperature below -35° C
  7. temperatureThe mixture was warmed to room temperature
  8. stirringstirred for one hour
  9. filtrationfiltered through Celite
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b4d9f5a00e294ca5b31e1de78e00a956
出典データセット
uspto-grants-1999_01
特許番号
US05856326

反応ノート

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